Syntheses,antitumour activities and antiangiogenesis of 1,2,3‐tris(ethoxycarbonyl)‐2‐propyl acrylate and its polymers

A new monomer, 1,2,3‐tris(ethoxycarbonyl)‐2‐propyl acrylate (TPA), was synthesized by reaction of acryloyl chloride and triethyl citrate. The homopolymer of TPA and its copolymers with acrylic acid (AA), vinyl acetate (VAc) and maleic anhydride (MAH) were prepared by polymerization using lauroyl peroxide (LPO) at 70 °C for 24 h. The structures of TPA and its polymers were identified by FTIR, ¹H NMR, ¹³C NMR spectroscopies, and elemental analysis. The number average molecular weights and polydispersity indices of the synthesized polymers determined by GPC were in the range 4200–23 000 g mol^?1 and 1.1–2.1, respectively. The IC₅₀ values of the synthesized samples against cancer cell lines were greater than those of 5‐fluorouracil (5‐FU). The percentage inhibition values of SV40 DNA replication were 82.2 for TPA, 34.3 for poly (TPA), 81.9 for poly(TPA‐co‐AA), 82.0 for poly(TPA‐co‐VAc), 35.6 for poly(TPA‐co‐MAH) and 12.7 for 5‐FU. The inhibitions of SV40 DNA replication and antiangiogenesis for the synthesized TPA and its polymers are much greater than those of the control. © 2001 Society of Chemical Industry